Derivative of pinene and process of making same.



UNITED STATES PigrEnT OFFICE.

NATHANIEL THUBLOW, OF NIAGARA FALLS, NEW Yo'R ASSIGNOR To I THE PORTCHESTER CHEMICAL COMPANY, or PORT oHEsr R, NEW YORK, A CORPORATION on NEW YORK.

DERIVATIVE OF PINENE AND PROCESS OF MAKING SAME- Patented Oct. 9, 1906.

Original application filed December 11, 1901, Serial No. 85,425. Divided and this application filed August 5,1902- Serial No. 118,482.

To all whom it may concern;-

Be it known that I, NATHANIEL THURLOW, a citlzen of the United States, residing at Niagara Falls, in the county of Niagara and State of New York, have invented new and useful Im rovements in Derivatives of Pinene and recesses for Producing the Same, of which the following is a specification.

This invention relates to a process for pro ducing pinyl oxalate and compounds containin the'same.

, In 1 mm No. 698,761, of April 29, 1902,

and No. 726,873, of April 28, 1903, I have disclosed a rocess of making camphor and a process 0 making dipentene, respectively.-

The invention described in the resent application relates to the same sub ect-matter patent and former specification above referred to.

To carry out the resent invention, I proceed in the manner described in the said patents, viz: I treat turpentine with oxalic acid' and obtain thereby a com 'lex oil mass, from which by suitable dist lation obtain pinlyl oxalate.

he following is a detailed description of my invention: Three hundred and fifty pounds of rectified and dehydratedtuipentine are heated with about seventy poun s of anhydrous oxalic acid to a temperature of about 120 centigrade or, preferably, to a somewhat lower temperature. When the .reaction ceases, the resultingoily roduct contains about two hundred ounds o dipentene, about six percent. 0 about three per cent. of, in oxalate, an

the remainder consists of so cam hor, borneol oxalate and formate, and t e higher polymerization products of pinene, with more or less free acid. The next step of the process is to wash the'mass' with water to re-' move this free acid. The resultant complex oil-may be storedfand' sold in that condition and serve asa basis for .the roduction of the other products. The spec c gravity'of this .oil is about .902, and itboils at 185 centi-' grade.- The resultant oily mass is then distilled at a low "temperature and pressure,

- [oily liquid'containing pinyl oxalate, pinyl (7882,c entigrade and vacuum of one-half atmosphere.) By successive distillations in this manner there is obtained as a residue an pinyl formate y formate,-together with polyterpenes and borneol 'formate. This residue is then distilled in a current of steam until'eight -five er cent. has been distilled. A colorless oi is thus obtained which becomes brownish on exposure to the air. The odor is harsh and unpleasant. This oil. has a specific gravity at 20 centigrade of .930.935. At 160 centigrade it begins to boil or decompose, and

.ninety per cent. distils over below 200 centid-ooonooo nc 330 i. a Having thus described my invention, the

following is whatl claim as new therein and desire to secure byLetters Patent:

1. The process of producing pinyl oxalate which consists in treating turpentine ,with oxalic acid under the influence of heat, distilling .the resulting mass, and collecting the residue after distillation. r

2. he process of producing pinyl oxalate- .which consists in treating turpentine with oxalic acid under the influencelof heat at a temperature below 120 centigrade distilling the resulting mass, and collecting the residue after,distillation.

3. The process of producing pinyl oxalate, which consists in treating turpentinewith oxalic acid under the infiuence'of heat, at a temperature below 120 centigradadistillmg the resulting mass at a temperature of from 7882 centigrade and vacuum of one-half atmoslphere, and collecting the residue.

. 4. he process of producing pinyl oxalate which consists in treating turpentine with oxalic acid under the influence of heat, distilling the resultin mass, and collecting the residue after distil ation', distilling said residue and collecting the distillatef." 'f' 5. The process of producing pinyl oxalate which consists in treating turpentine with oxalic acid under the influence of heat, dis-. tilling the resultin mass, and collecting the residue after distil ation, distilling said resi-' due in a current of steam u'ntileighty-five per cent. to ninety er cent. thereof comes over, collecting said istillate."

6. The process of producingpinyl oxalate which consists in treating turpentine with oxalic acid under the influence of heat,v at a temperature below 120 centigrade, distilling I the resulting mass at a temperature of-from 78-82 centigrade and vacuumof one-half atmosphere, collecting the residue, distillin said residue in a current of steam untl eighty-five per cent. to ninety per cent; thereof comes over, and collecting said distillate.

, 7. The herein-described oily mass containin pinyl oxalate having a harsh unpleasant odbr and becoming brownish on exposure to air, a specific gravity of .930 to .935 at 20 centi rade.

8. he substance by the action of oxalic acid on tur entine and having the formula: C H ,,(C OH ,said compound having a-boiling-pomt of about 157 to 160 at six hundred and eighty -millimeters vacuum, breaking u on heating into camphor, carbon monoxi and water,

' and on heating with water-into oxalic acid and hydrocarbons.

M I, NATHANIEL THURLOW.

V Vitness'esu i 1 Laws E. Smmnnns,

ARTHUR G. Baormam pinyl oxalate, produced 

